Formamide → HCID 178470647, compound

HRID 1503894Notes

Reaction equation

[NH2:1][C:2]1[S:6][C:5]2[CH2:7][CH2:8][CH:9]([CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:4]=2[C:3]=1[C:16]([O:18]CC)=O.[CH:21]([NH2:23])=O>>[OH:18][C:16]1[C:3]2[C:4]3[CH:9]([CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH2:8][CH2:7][C:5]=3[S:6][C:2]=2[N:1]=[CH:21][N:23]=1

Participants

Reactant 2

HCID 713Formamide

HCID 59379370HCID 59379370, compound

Product 1

HCID 178470647HCID 178470647, compoundYield 43%

Conditions

Temperature: 180 °C

Procedure

To a 10-L 4-necked round-bottom flask, purged and maintained with an inert atmosphere of nitrogen, was added a solution of 15.2 (500 g, 1.68 mol, 1.00 equiv) in formamide (5 L) at room temperature. The resulting solution was stirred for 5 h at 180° C. in an oil bath. The reaction mixture was cooled to room temperature and then quenched by the addition of 10 L of water/ice. The resulting solution was extracted with 3×5 L of ethyl acetate and the organic layers were combined. The mixture was washed with 3×3000 mL of brine, dried over anhydrous sodium sulfate and concentrated under vacuum. The solids were collected by filtration to afford 200 g (43%) of ethyl 2-[12-hydroxy-7-thia-9,11-diazatricyclo[6.4.0.0^[2,6]]dodeca-1(8),2(6),9,11-tetraen-3-yl]acetate (15.3) as a yellow solid.

Workup

customTo a 10-L 4-necked round-bottom flask, purged
temperaturemaintained with an inert atmosphere of nitrogen
temperatureThe reaction mixture was cooled to room temperature
customquenched by the addition of 10 L of water/ice
extractionThe resulting solution was extracted with 3×5 L of ethyl acetate
washThe mixture was washed with 3×3000 mL of brine
dry with materialdried over anhydrous sodium sulfate
concentrationconcentrated under vacuum
filtrationThe solids were collected by filtration

Sources & evidence

ORD record: ord-33a1a2ce54cc4307ae09c2affed78d35
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09212190B2

Reaction notes

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